Wearing this today though this is from the "straps on the Vaer" experiments from a week ago. This is a Christopher Ward leather that came with my C63. It's a high quality but really pretty stiff strap. Any pointers on breaking in a new strap, besides "uhm, just wear it Keith."
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Just work the strap back and forth for a while when you are watching TV or something. Just like breaking in a baseball glove. Should be good in no time at all.